Surface active galacturonic acid derivatives

The galacturonic acid derivatives of formula: ##STR1## R1 being a linear or branched alkyl having 2 to 22 carbon atoms, R being: ##STR2## for which the carbon carrying the hydroxyl group is attached to the endocyclic oxygen atom.R2 being hydrogen, R1, an alkali metal atom, an alkaline-earth metal atom or a quaternary ammonium group of formula: ##STR3## in which R3 to R6 is each independently of the other hydrogen, an alkyl having 1 to 6 carbon atoms or a hydroxyalkyl having 1 to 6 carbon atoms, are surface-active agents.

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Claims

1. A galacturonic acid derivative having the formula ##STR16## wherein R1 represents linear or branched alkyl having 8-22 carbon atoms, and

R represents ##STR17## or ##STR18## wherein R2 is the same as R1 and wherein the carbon atom carrying the hydroxyl group is not attached to the endocyclic oxygen atom.

2. The derivative of claim 1 wherein R1 is alkyl having 14 to 22 carbon atoms.

3. The derivative of claim 1 wherein R1 is alkyl having 8 to 14 carbon atoms.

4. The derivative of claim 3 wherein R1 is decyl.

5. A process for imparting surfactant properties to a composition comprising incorporating into said composition from 0.1 to 60 percent by weight a derivative of the formula ##STR19## wherein R1 represents linear or branched alkyl having 8-22 carbon atoms and

R represents ##STR20## wherein R2 is the same as R1 and wherein the carbon atom carrying the hydroxyl group is not attached to the endocyclic oxygen atom.

6. A detergent composition comprising 0.1 to 60 percent by weight of a detergent and 99.9 percent to 40 percent by weight of adjuvants, said detergent comprising a galacturonic acid derivative having the formula ##STR21## wherein R1 represents linear or branched alkyl having 8-22 carbon atoms, and

R represents ##STR22## wherein R2 is the same as R1 and wherein the carbon atom carrying the hydroxyl group is not attached to the endocyclic oxygen group.

7. The detergent composition of claim 6 wherein R1 is alkyl having 8 to 14 carbon atoms.

8. A cosmetic composition comprising 0.1 to 50 percent by weight of an active substance and 99.9 to 50 percent by weight of an excipient, said active substance comprising a galacturonic acid derivative having the formula ##STR23## R1 represents linear or branched alkyl having 8-22 carbon atoms, and ##STR24## wherein R2 is the same as R1 and wherein the carbon atom carrying the hydroxyl group is not attached to the endocyclic oxygen group.

Referenced Cited
U.S. Patent Documents
3873614 March 1975 Lamberti
4335236 June 15, 1982 Tsuyumu et al.
4713447 December 15, 1987 Cotton
4950743 August 21, 1990 McCurry Jr. et al.
5079350 January 7, 1992 Fujita et al.
5166337 November 24, 1992 Ripke
5223411 June 29, 1993 Plusquolke et al.
Foreign Patent Documents
334498 March 1988 EPX
326673 August 1989 EPX
427210 May 1991 EPX
Other references
  • Bocker et al, "Synthese und Eigenschaften von Kohlenhydratensiden", Tenside Surf. Det. 26 (1989) 5, pp. 318-324. Hui et al, "Synthesis of glucoside surfactants and asymmetric reduction of phenyl alkyl ketones in chiral micelles", Chemical Abstracts, vol. 109, 1988, Abstract No. 190679t. Namba et al, "Liposomal modification with uronate, which endows liposomes with long circulation in vivo, reduces the uptake of liposomes by J744 cells in vitro", Life Sciences, vol. 50, 1992, pp. 1773-1779.
Patent History
Patent number: 5688929
Type: Grant
Filed: Feb 18, 1993
Date of Patent: Nov 18, 1997
Assignees: Agro Industrie Recherches et Developpements (A.R.D.) (Paris), Zschimmer & Schwarz GmbH & Co. Chemische Fabriken (Lahnstein)
Inventors: Serge Petit (Montmaco), Robert Ralainirina (Amiens), Serge Favre (Compiegne), Regis De Baynast (Versailles)
Primary Examiner: David M. Naff
Assistant Examiner: L. Blaine Lankford
Law Firm: Cushman Darby & Cushman Intellectual Property Group of Pillsbury Madison & Sutro LLP
Application Number: 7/975,546
Classifications
Current U.S. Class: Viscosity Or Degree Of Polymerization Changed (e.g., Degrading, Cross Linking, Etc.) (536/41); 536/185
International Classification: C07G 300; C07G 1100;